Kick off your adventure with a late-afternoon private boat cruise through the towering cliffs of the majestic Sumidero Canyon 🚤, soaking up the golden-hour magic after a traditional lunch in colonial Chiapa de Corzo 🍲.
Next, journey into the highlands to explore the vibrant, colourful streets of San Cristóbal de las Casas 🌈. Dive deep into living indigenous heritage as you witness the profound mysticism inside the church of San Juan Chamula ⛪, and share a warm, home-cooked meal with a Tzotzil women’s weaving cooperative in Zinacantán 🧶.
Trade the cool mountains for the tropics and climb the colossal, terraced acropolis of Toniná 🏛️, one of the Maya world’s most powerful ancient cities. We’ll then hit the road for the stunning Cascadas de Agua Azul 💦 to swim in turquoise pools and fall asleep in rustic eco-cabins by the water. After walking behind the dramatic curtain of Misol-Há 🌿, we’ll set up our fully equipped jungle camp near Palenque ⛺.
Cap off the expedition by beating the crowds at the legendary Palenque ruins 🐒, hiking hidden trails to uncover ancient Maya secrets under the lush canopy. Finish with a relaxing afternoon by the pool 🍹 before your seamless onward journey from Villahermosa. Canyons, waterfalls, living cultures, and jungle camping—this is the ultimate overland adventure! ✨🇲🇽
* ✈️ Travelling as a private group on the same flights? We’re happy to tailor the first and last days of the itinerary to maximise your adventure as soon as we know your flight details! 🗺️✨
As a general reference, our private comfort departures average the following rates:
👥 Couples (2 travellers): Approx. $480 USD per day, per traveller
🛞 Small Groups (4 travellers): Approx. $320 USD per day, per traveller
🚐 Medium Groups (6-7 travellers): Approx. $230 USD per day, per traveller
🚌 Large Groups (8+ travellers): Approx. $200 USD per day, per traveller
🔑 Rates are based on double occupancy.
👧 Travelling with kids? Enjoy a 10-15% discount for children under 12 sharing a double-bed room with parents.
Ready to tailor this journey? Use the Enquiry Form in the sidebar to share your group size and rooming preferences, and we will build your custom quote!
We had a wonderful 10-day family trip through Chiapas with Jaime from Lupita Overland, travelling from Oaxaca City through Tehuantepec, Juchitán, Tuxtla, San Cristóbal, Palenque and back, with plenty of stops along the way.
Jaime was considerate, flexible and very helpful from the start. It was clear how much he loves Chiapas, and he was genuinely excited to show us around, which made the trip feel much more personal. We visited caves, gorges, waterfalls, ruins, local food places and cultural spots, and felt we were able to see a lot without the days becoming too much.
We travelled as a family with our 5-year-old son, which was a new type of trip for Jaime, but it worked really well. The itinerary was full, but not over-packed. There was still time for our son to rest, play and swim in the hotel pools, and the longer driving days were broken up with good stops, so the travel never felt too hard.
The van, Lupita, was spacious, comfortable and well-equipped, and the hotels Jaime arranged were lovely throughout the trip. We always felt safe and well looked after, while still feeling like we were having a proper adventure through a really beautiful part of Mexico.
Overall, we thoroughly enjoyed the trip and are very grateful to Jaime for making it such a memorable experience. We’d happily recommend Lupita Overland to anyone wanting to explore Chiapas or other parts of Mexico in a comfortable, flexible and personal way.😎
Our family of three, including our 5 year old son, has just returned from an epic 10 day road trip with Jaime in his awesome Lupita van. A round trip from Oaxaca to Chiapas and back to Oaxaca, with so many beautiful, interesting, and memorable stops along the way.
This was a fantastic family friendly tour of Chiapas region. Jaime created a journey that gave us a wonderful mix of nature, culture, history, food, and local experiences. We visited dramatic canyons, caves, waterfalls, community villages, local markets, colonial cities, archaeological ruins, cultural festivals, traditional handicraft workshops, and places to try delicious regional food and drinks. It was exactly the kind of trip we hoped for: full of adventure and variety, but still paced well enough for travelling with a young child.
Jaime was excellent from the very beginning. He was organised, communicative, flexible, and thoughtful throughout both the planning and the trip itself. He is especially good at setting and managing expectations, which made the whole experience feel smooth and relaxed. We always knew what to expect, but the trip still felt personal and full of discovery.
What made the experience really special was Jaime himself. He is calm, kind, and great with families. He works respectfully with local communities and clearly has a deep love for Chiapas and the people, landscapes, traditions, and culture of the region. It was a joy to have him share his knowledge, experience, and passion with us.
We also now know that Jaime covers trips through many other regions of Mexico, as well as some parts of Central America, which makes Lupita Overland a great option not only for Chiapas, but for anyone looking for a private, flexible, and meaningful overland travel experience more broadly.
We highly recommend Jaime and Lupita Overland to anyone looking for a private or small group tour operator, family road trip, overland tour. We would absolutely travel with Jaime again and hope to do more trips with him when we return to Mexico.
This tour was the most incredible experience! Jaimie, the tour leader, is the dream tour guide. Super organized, a really well paced tour. Many activities, but also some down time. He even gives very detailed suggestions for great things to do in free time. Jaime provides a written schedule of the itinerary in advance, as well as a daily meeting informational and patiently answers all questions, both in advance, and on the fly. He is super focused on everyone’s comfort and safety, continually checking in to make sure all is well. Jaime skillfully maneuvers the van over large speed bumps, through twisty mountain roads and around congested city streets, all with a smile on his face. Every person Jaime encounters becomes his amigo- he puts the national police guards at ease, they wave him through checkpoints, and hosts of our planned activities greet him with hugs. He has an incredible ability to connect with everyone, which I especially appreciated since I don’t really speak Spanish. You couldn’t be in better hands. We were fortunate to also have another amazing tour guide, named Cassie. She is also super knowledgeable about the areas we visited and she actually writes a great blog as Mexico Cassie. She was also fluent in Spanish and full of great recommendations and lots of common sense advice. Because of our guides area knowledge and great planning, we got to places before the crowds, had fabulous informative licensed guides for ruins tours, enjoyed great local cuisine, and stayed in off the beaten path gem accommodations. I wish I could give it 10 stars !
Traveling with Lupita Overland was amazing!! The group I travelled with was a great mix of people, and everyone was participating to achieve a fun and memorable experience. We saw so much of Mexican culture, and we experienced so much of the rich culture as well. I had never been on a tour like this before, and I was a bit nervous for it, but within two days on tour, I felt comfortable with Jamie and Cass, I was on the Mayan Tour Mexico Cass Edition. I would do this tour again in a heartbeat. We saw Spider Monkeys drinking from a Cenote, listened to Howler Monkeys at Calakmul while we explored and climbed…I attempted to climb….at the Maya Archeological Site in the middle of the jungle, and met amazing people who shared their cultural traditions with us. I think I’ll be on another Lupita Adventure in no time. Thank you Jamie and Cass for an amazing and memorable experience!
I just finished a 12 day trip with Lupita from Chiapas to Quintana Roo, Mexico. Jaime’s experience and professionalism as a trip organizer is obvious in his planning, attention to the needs of his guests and his relationships with local guides. We visited a wonderful range of natural, archaeological and cultural sites and learned so much about the areas we traveled through. We had deep conversations and lots of laughs. It was an amazing trip.
Quick heads-up: This video is just a teaser! Not all activities shown are included, and some of this trip’s best highlights aren’t even in the footage. Check the day-by-day itinerary below for the exact plan! 
